To Ride Around In Circles
by Acajou Amarth
Summary: When money runs out again and Dad is nowhere to be found, sixteen year old Dean knows the fastest way to make good money. So what if it's a bit distasteful? But he didn't expect this guy, the one with the sad blue eyes and the weight of the world on his shoulders. He also didn't expect to actually get turned on. Destiel oneshot. Angsty, smutty, comes with underage warning.


**_Disclaimer:_** _I can't claim the show would be better if I was writing it, because no episode would never get done._ It's astounding this fic did.

 _ **Rating:**_ _M_

 _ **Warnings:**_ _Dean is underage. He's also whoring himself out in order to be able to feed his brother. Despite that, this might be the hottest thing I've ever written._

To ride around in circles

It's been a hot afternoon of sizzling Arizona heat, just hot enough that it's still balmy when the sun has set. This is a good thing, Dean knows. Arizona seems a good place for work like this. Really low on the demon front, and so far, nothing supernatural has shown up in the vicinity of their particular spot.

Dad left them here two weeks ago, with enough bills to cover the motel and a bit of food, and while he checks in regularly, the last call Dean got was him saying the hunt is taking him longer than expected. Dean didn't mention they're running out. He never does. He's old enough to take care of this himself.

It's bad enough he's stuck babysitting an increasingly frustrated 12-year-old who'd much rather be at a high school somewhere. He loves the kid, he does, but Dean would prefer being on a hunt somewhere with Dad instead of telling his little brother to keep the doors locked while he's out and having no choice but to trust the kid to follow through. Sam knows how important it is that he stays safe, though. He'll huddle up inside with a book or twelve and have a good sulk about his life. Nothing bad will happen while Dean is away.

Dean, of course, will come home around four in the morning, knock four times, pause, knock three times and once Sam lets him in, act a bit drunk – if work is good tonight, actually be drunk – and boast about hustling and girls.

The thing is, while there are girls in Nowhere, Arizona, it's a bad crowd for hustling pool. Just doesn't seem to be their game most of the time, and if it is, they look on the prowl to rob a newbie of his money regardless of whether they won or not.

So standing in an alley in a thin white undershirt and ripped up jeans it is. It's not like it's the first time. And it's not like it's so bad. Usually, all he has to do is spend some time on his knees. He'll get through it and Sammy will be fed and with a roof over his head another day. Depending on how good it goes, maybe the full duration until Dad comes back. Maybe there'll even be enough to get Sam a copy of that damn Shakespeare play he's been obsessing about.

It's not long into the night till some guy approaches him, some redneck who looks torn between wanting to fuck him and to fuck him up. Dean knows how this goes and when his knees are in the dirt and a dick is forced down his throat, he pretends to be utterly helpless and lets his face be fucked. Throws in a couple of choking sounds and wide, frightened eyes just to please the guy. Thinks about being able to bite that dick clean off if the guy actually gets too rough. Thinks about buying himself a beer after this and washing away the taste. The bar around the corner doesn't look like the kind that presses for ID.

In the end, he doesn't even have to swallow. The guy pulls out, pushes Dean away against the brick wall and comes messily, but thankfully onto the ground. He grunts, puts himself away again while Dean catches his breath, then throws a couple of dollar bills in Dean's direction. Dean counts sixteen bucks, which is less than his asking price, but close enough for him not to risk a brawl. The guy leaves with little more than a disgusted sneer at him.

Dean gets up again, brushes the dirt off his pants and puts his shirt back in place.

Now for that beer.

* * *

The only thing better than a cold, fresh brew after a really nasty blowjob is getting away with buying it. Dean has no illusions about his looks. Maybe he can pull off eighteen, but even if he wasn't in deliberately jail-baity whore getup, twenty-one is a far-off dream. Maybe then, Dad will let him go on a solo hunt.

For now, he has to work with what he's got and looking like a fucking twink is pretty much the best thing that could have happened to him. That and bartenders who don't give a fuck so long as you have the money.

The first sip is barely suitable to wash down the taste. The second sip is as close to heaven as he gets.

"I'll pay for this", a rough deep voice next to Dean says and Dean is momentarily distracted by the wad of money the guy is pushing towards the bartender. Not only is it a shit load, but it's also like the guy has no idea that it's a shit load. The bartender raises an eyebrow and picks his bills of the heap – taking a bit too much, Dean notices – and Dean follows the guy's hands as they push the money back into the pockets of his tan trench coat. Geez, if this guy isn't interested in buying sex, Dean might just pickpocket him.

"Thanks", he says and puts on a slow smile. The guy isn't so bad, as far as customers go. Messy dark hair, a nicely-cut face, good enough built from what Dean can gather, and a pair of sad blue eyes. If Dean had a type of guy, this one would probably do the trick.

"I appreciate it", he adds and lightly strokes the neck of the cold, humid bottle over the curve of his neck, just subtly enough not to be blatant, but just blatant enough to be not subtle. Then puts the bottle to his lips and takes a sip.

The guy doesn't react. He barely even looks at Dean at all. His focus is straight ahead, eyes dark with something. The bartender unbiddenly places a beer in front of the guy, too, and he raises it to his lips without even blinking. They're pale, those lips, especially amid the dark stubble and when they wrap around the bottleneck, Dean actually for a second considers taking this guy somewhere without charging.

Which he isn't going to do, of course. He's straight, after all, and the only reason he's doing shit like getting hit on by male strangers in bars is to feed his brother.

"I guess I should tell you I'll cost you", he casually says, more to remind himself than to actually inform the guy.

They guy's shoulders slump and his sad blue eyes actually seem to grow sadder.

"Yes, I've noticed."

"But tell you what; I'll make you a good price. Handsome guy like you. It'll be fun."

The guy only nods and Dean takes a gulp of his beer. Well, whoever he is, he doesn't seem to be very talkative. He wonders if that means he should shut up, too.

"I'm Dean, by the way", he ends up saying and then wonders why the fuck he'd even say that. The guy didn't ask and the last thing he needs is for some undercover cop (which might very well be the direction this is taking) to have a way of tracking him down once he inevitably escapes before non-sexy handcuffs come anywhere near him. "Unless you want to call me something else."

"Why would I want to do that?"

The guy seems genuinely puzzled by the concept and it throws Dean off a little. For some reason, he feels prompted to explain, even though he feels stupider by the sentence and his fake casual tone can't possibly be fooling anyone.

"I don't know. Some names are just sexier, I guess. And some guys want to pretend it's the guy from work they'd rather be fucking."

Good job, Dean, mention the fact that you have other clients. Number one rookie mistake and he is far from a rookie. Something about this guy is unnerving. At least he doesn't seem to mind. The grip on his beer gets a little tighter, but at least he doesn't look pissed off.

And those are good hands. Strong, a little rough looking. Like they could be heaven on an eager dick. Fingers the perfect width for fingering him op-…

"Or a celebrity, I guess", he finishes a little lamely, still staring at the way those fingers are wrapped around the bottleneck, more than a little irritated by the interest his dick is starting to take in this guy.

"I would never want to pretend you're anyone other than you."

Still trying to build up both his wit and his guard, he's caught seriously off the second by the intensity of that gaze, suddenly pinning him in place.

"That's cool, dude," he stammers, "whatever you want."

The man never breaks eye contact while he finishes his beer and Dean almost subconsciously follows suit. It's good and cool down his throat and he's silently thanking the bartender for not giving a shit about underage drinking, because otherwise he'd be wholly occupied with the slow heat, the sad longing he sees in this guy.

Maybe he should sit this one out. Just go back outside, wait for his next mark. All the money in the world does not seem worth the emotional baggage this dude seems to carry around with himself.

But then he breaks the gaze to follow his beer back to the counter, where he puts it down with finality Dean can't help but echo.

"I would like to leave this place now."

And suddenly, Dean can feel the ground again, the walked-through floorboards beneath his feet as he hops off his bar stool and almost laughs in relief.

"That, my friend, is the best idea I've heard all night."

Because this, he understands.

* * *

They don't go to the same alley, which is more than alright with Dean. In fact, the guy is walking ahead of him for quite a while until they've reached the outskirts of the admittedly small town. Then he just sort of stops and looks at the sky for a bit. Dean allows himself the luxury of following his gaze. The dude seems to be on his own time anyway.

It's a clear night and for a second, Dean is reminded of sitting outside with his mom that one evening and her showing him every constellation she knew. He even remembers some of them. Even when you're four, one of the last conversations you've ever had with your mom kind of sticks with you.

Absent-mindedly, he starts babbling and the guy's gaze comes to rest on him.

"So, what can I do for you? Blowjob? Hand? If you ask nicely, we can talk about doing more."

And what the hell is he doing basically offering his ass? He doesn't do that, not unless absolutely necessary. Right now, it's nowhere near necessary. The guy looks like he'll take what he can get, no ass-action involved, and pay good money for it, too.

Must be the whole thing where it'd keep Dean off the streets for a while, maybe even for the next time Dad is gone too long. The guy's certainly well-off and he probably wouldn't object to spending a bit more than Dean's normal asking price. That would be well worth a little ass-action.

It's definitely not the fact that he's actually getting kind of turned on under this guys unrelenting stare.

He doesn't say anything. Which is actually kind of a shame, seeing as it wasn't the worst sex voice from what little the guy had said at the bar. It also doesn't give Dean any pointers as to what the guy actually wants.

"I guess we can get started with some kissing, huh? Unless you're not into that."

Dean doesn't usually offer that, either, but the guy seems kind of lost and it pretty much isn't a hardship to equal the thought of those lips on his with _not so bad_. A bit chapped, but he can work with that. Besides, he's never been the kind of sap to think of kissing as too intimate. If it's what it takes to make a guy lose his cool, why the fuck not?

"Oh I am "into that""- Jesus fuck, there were actual air quotes – "but I don't think-…"

"You know what I think, dude? I think you think way too much."

And without much hesitation, he pulls the guy down on his lapels to press his lips against the man's lush but chapped lips.

For a second, the way the guy almost hesitantly presses back is almost endearing. Then Dean adds a good lip-nibble and suddenly, his back is against the wall of the nearest house and the guy is ravaging his mouth and chapped suddenly becomes incredibly erotic when it's against the underside of his jaw line and down his neck, then back to bruise his lips in the best possible way.

"Shit, you're good at that", he moans when the guy starts sucking on his pulse, and while it's certainly something Dean is only adding for effect, he can't deny that for the first time, he means it. He also doesn't mind that he'll almost certainly be running around with a huge hickey at a very visible place for at least five days and that, should the guy decide not to pay, this'll tick other customers off. "Don't stop."

The guy seems to become aware of the position he's put Dean in, flush against the wall, head tilted back and panting.

"I'm sorry, Dean, I didn't mean to-…"

"Don't apologize." His own voice sounded huskier than he remembered it being. "Give me more where that's coming from and we'll forget about money altogether."

And fuck, he almost means that. He knows his grin is saying he means that. He knows no one can resist that grin, even when it's fake. Which it really should be right now and seriously isn't. He might not be into guys, but this might very well turn out to be at least as good as hooking up with a random girl would have.

Thankfully, it doesn't take much persuasion to get that mouth back on his, hungry and a bit out of control and leaving him aching for action in all the right places. Hands – rough, strong, perfectly steady, like he thought – are on his naked shoulders, the back of his neck, his lower back, pulling him closer.

His hands automatically go to work on the guy's zipper.

"Wait", the guy gasps against Dean's ear and his hands are pinned against the wall on either side of his hips.

And then he actually slides to his knees in front of Dean.

If he hadn't been well on his way to hard as nails before, this would have done the trick. Which is good, he reminds himself, because while it's never happened that a customer has actually wanted to go down on him, he's pretty sure lack of arousal would have killed any chance of making money off him. After all, that is the goal here.

Make money, buy Sammy that stupid book, have enough for groceries and rent.

The fact that he actually is turned on like crazy by this guy is a pretty awesome bonus. And his dick hasn't gotten any attention lately other than his own, which must be why even a guy manages to make him this hard.

Though he lets go of Dean's wrists – Dean almost wishes he didn't, there was something both erotic and treasuring in the feeling of those rough hands holding him steadily and tightly in place – it is implied they stay at Dean's sides and he actually keeps pressing them tightly against the concrete surface of the wall.

The guy opens Dean's pants without even looking; his eyes are focused completely on Dean's face. And who the fuck has eyes like that anyway? Even in the dim light of a far-away street lamp, Dean can feel the intense blue as much as he can feel stubble on his hip bone as soon as he's stepped out of his pants.

Still without looking away, the man's hands press against Dean's hips in a way that both calms any and all existing nervousness and is sure to drive Dean wild, then first kisses the skin right below Dean's belly button – and shit, since when does that feel anything but silly – and then there are gorgeous lush lips wrapped around Dean's dick.

Dean hits his head on the wall hard enough to see more stars than before.

"Fuuuuck", he breathes out and the guy starts using tongue. Dean feels every muscle in his body go taunt. His wrists press harder against the wall from the sheer difficulty of not grabbing the guy's hair and guiding the slow motions he starts with his head, sucking harder at the tip of Dean's dick while tonguing that heavenly place just below the head.

And then, without warning, he is being swallowed down throat deep and his hands go into that thick, soft hair on their own account and just… hold on. And instead of complaining, the guy grins somewhat filthily around the base of Dean's dick and starts _humming_ in approval.

"Fuck, fuck, fuck, shit you are so good at that, this is so-… ah!"

Hands on his hipbones anchor him as the guy slowly starts to pull off and then slide down again, slowly encouraging Dean to fuck his mouth.

This is hands down the best blowjob he's ever gotten. Forget about every other mouth he's ever had on his dick – nothing compares to this strange sad dude in his trench coat, with those blazingly blue eyes and the heat inside them, the softness of the inseam of the guy's lips when he pulls off enough to just French the head for a while, the absolutely incredible feel of being buried balls deep in a hot throat, feeling the guy swallow around him again and again, the slide of his strong tongue up and down his dick, up and down and up and down, all the while sucking so hard Dean feels like he might explode any second now.

He is standing with his back pressed against a random house, looking out at the desert at night, at the silhouette of canyons before a night sky so full of stars he can almost see one falling and if he doesn't stop this right now, he will come right now. But looking back at the man's eyes, at the lips stretched around his dick does not exactly help.

"Hold on, hold on-…" With a wince, he pulls out of the guy's mouth. "If you don't stop right now, this'll be over before you get to have any fun at all."

And why, why, why is he putting a stop to this again? For a few seconds he just closes his eyes and searches his brain for a reason that isn't wanting this to not be over yet. He settles on: Because no one can be expected to pay for giving head, right?

"But I'm having fun, Dean. By all accounts, I'm having far more fun than I should be."

And he goes right back to sucking Dean down like there's no tomorrow. And everything in Dean screams to just let him, he's so close, he's so close-…

"No, seriously, I want this to be good for you, too", he chokes out and the guy lets up with a groan, forehead buried in Deans stomach, his breath still hitting Dean's dick in the most tantalizing way, puffs of heated air bathing him, depriving him, bathing him, depriving him, a constant tease of the orgasm he could have had. Fuck, why didn't he just let him-…

"It _is_ good for me", the guy says, voice sounding so fucked Dean almost comes from the sound alone. But he does lift his head and _look_ at Dean.

And fuck. Fuck.

"You know", Dean says hoarsely, "there's lube in my pocket. If you want-… If that's something you'd be into, you could fuck me."

"Yes, Dean. I'd be very into that."

There are no air quotes this time. Instead, there's a look so heated it has Dean actually whimpering. Dean sees himself walking out of this having earned absolutely no money and he's so fine with it he can't even start mentioning costs.

"I'm not prepped or anything, but it shouldn't take long."

The guy merely reaches for Dean's jeans that lie pooled around his ankle and pulls out the lube without ever looking away from his eyes. Dean takes the bottle from him with shaking hands, steps out of his pants and quickly spreads enough lube to start with on his own fingers. The guy actually sinks down to sit on his heels, now watching Dean's hand with a hungry sort of look.

Fuck. He's actually going to watch.

Dean can't even begin to put on a show, he needs to feel a finger inside him so bad. Without much ceremony, he spreads his legs enough to be able to reach back and pushes two finger against his overheated rim.

He hisses as he circles a few times, fingertips putting just enough pressure on it at the same time, never looking away from the guy's face as he watches with an absolutely wrecked look on his face.

One finger sinks in a lot sooner than he can bear when he's alone in the shower and telling himself it's not gay to put knowledge on pleasure points to good use. It's a brilliant burn and he's barely even touched his prostate once before he begins slipping in the second finger, too.

And fuck, that's too fast, it actually hurts, but it's so good he has to close his eyes and press his head back against the wall to keep himself still. He's still adjusting to two fingers not even knuckle-deep when the bottle of lube is taken out of his free hand and after the click of the cap and a familiar slick sound, a third finger starts stroking against the place where his own disappear inside him.

His eyes fly open as the guy licks the long line of weeping pre-cum from the base of Dean's dick to the tip and presses in next to his own fingers at the same time.

"Fuuuck", he swears and as quick as he can, his free hand is in a tight circle around the base of his dick, barely in time to keep him from coming. "Fuck, fuck, fuck", he keeps chanting as the guy's finger pushes in and Dean's fingers sink in further in the process.

When he slowly starts a rhythm, all three fingers moving in deeper and deeper with every stroke, the guy's finger very deliberately rubbing against Dean's prostate with every single stroke, Dean feels just about ready to pass out. When the guy actually presses another finger against Dean's already stretched rim, Dean snaps.

"Okay, enough! It's enough, I'm prepped enough!"

"Are you sure? It might still hurt."

Ah, fuck, he forgot how fucking orgasmic that voice sounds.

"I'm in fucking pain now and do you see me complaining? Get inside me, get inside me now!"

He swears as all three fingers slip out, still desperately holding off orgasm with his other hand. The guy finally gets up, but not without stealing another lick at the head of his dick and finally, finally gets to work on his pants, Dean's lube-streaked fingers fumblingly helping to get the zipper and underpants down.

And shit, the guy was right, with a dick this fat, it will hurt. Dean can't wait a second longer.

Fortunately, it seems the guy can't either. With one fluid motion, Dean is being lifted and impaled on inch after inch of glorious dick.

(Dimly, it registers that this kind of thinking will probably throw him for a serious loop when he has to figure out if loving having a big dick shoved up his ass might not mean he's a tiny little bit interested in guys.)

The intense burn is enough to stave off orgasm when the guy drags Dean's hand away from its secure place at the base of his dick and instead interlaces their fingers and presses the back of Dean's hand against the wall next to Dean's head.

For a small, endless moment there is nothing but the solid thickness of the guy's dick in his ass and his shuddering pants in Dean's ear.

Then he moves and the pleasure is enough to almost knock him out.

Thrust. Dean can hear his own heartbeat galloping away inside every single extremity.

Thrust. He is one with his pulse, one with the dick pulsing inside him.

Thrust. He is coming so hard he can't even scream.

Thrust, thrust, thrust. A sudden rough hand against Dean's dick milks him through the shocks of constant attacks on his prostate.

Thrust. Thrust. The guy comes with a sob of Dean's name, buried so deep Dean's feet don't even touch the ground any longer.

A mouth against his, lips against lips, shared uneven breath. One last, sloppy, heartbreakingly tender kiss.

And then they both still.

* * *

Awareness trickles in like a beast from the underground. It's the serious ache left behind by a slipped out, suddenly flaccid dick. It's the pain in Dean's shoulder blades where he slammed against the wall. It's the sudden realization that they didn't even use a rubber and the thought that this might be on the edge of town, but that they weren't even quiet.

It's the suddenly quickening breath of the man who just actually fucked his ass and being suddenly without the warmth and protection of having that man pressed against him. It is the quiet, terrible 'no, no, no' as the man tucks himself back into his pants and Dean belatedly realizes he should probably get dressed as well.

His legs almost fail to hold him up and it takes him four tries to get his shaking hangs under control, but he still manages to do up his pants.

His throat feels tight suddenly, tight and dry. He gingerly bends over to pick up the bottle of lube still lying on the ground. He is uncomfortably sweaty and leaking in places he never wanted to feel like he might be leaking.

And the man appears to be having some sort of panic attack.

"I shouldn't have interfered. You were going to get arrested tonight if I hadn't distracted you, so I thought-… But I didn't mean to take it this far. I only meant to-… You've been dead for so long. I was supposed to look out for you, not-… Not this."

Dean's thoughts are still slow enough for it to take a few seconds before the words register and the massive cold front hits him with deadly precision.

"What?"

"It's been so long that I should be used to it, but every day, every century, every celestial minute, I miss you. I guess that's what love is. Missing someone for the rest of your miserable existence. It's no wonder our father discouraged us from that notion."

Suddenly, Dean wishes he had brought a gun, because that cold front is freezing his very insides.

"Okay, dude, I've heard a whole lot of guilt trips, but whatever you're on about – I'd rather have one of those that end with my head bashed against the wall and my ribs kicked in, because you're getting seriously creepy."

"I'm sorry, Dean, I didn't mean to frighten you. You should get back to Sam now. I assume this is enough money to last you a while."

The man holds out the entire wad of money he previously handed to the bartender and then some, but taking it is the last thing on Dean's mind right now.

"How'd you know about Sammy?"

The cold front is fucking ice inside his voice now.

"Dean-…"

"Have you been spying on us? Have you-…", he sputters for a few second before the ice is properly formed into a weapon. "Have you been perving on my little brother, you worthless fuck?"

"No, Dean, I didn't-…"

"Because it seriously sounds like it. I don't know who you think you are-…"

"I'm your friend, Dean. Please-…"

"-… but you should fuck off before I come up with a very creative way of killing you. Killing a human would be a first, but I'll do it. And I won't do it quick, either. I ever see you around my little brother or me again, you'll find out just how good I am with a knife and fire."

The man finally stops coming closer or holding out a placating hand or whatever it was he was doing this entire time.

"I understand." He seems to swallow and some terrible left-over arousal makes Dean watch the up and down of his Adam's apple. "I won't bother you again. This was wrong. This was so wrong, but I couldn't-… You didn't get arrested tonight and you'll wake up with enough money in your pocket to more than last the two of you until your father comes back in two weeks. I suppose that should make me feel better."

Whatever warped logic that guy is following, it doesn't look like it's making him feel much better. If anything, he seems more downtrodden than ever. Not that Dean so much as pities him. Whatever it is he's feeling bad about, it's not gonna make Dean feel any less creeped out. Slightly disgusted, too. To think he let that guy anywhere near his ass, let alone in it-… And to have enjoyed it, too… He can already see himself vomiting back at the motel.

"Goodbye, Dean."

Between one blink and the next, the guy is standing next to Dean without having moved at all and is putting two fingers against his forehead.

* * *

Dean wakes up feeling more rested than ever. And it's light out. More than light, judging by the heat, it's mid-afternoon.

"What the hell," he grumbles into his pillow. "How long did I sleep?"

"You slept through the whole morning, jerk. And just so you know, I ate the last of the cornflakes."

Sammy is sitting at the table, reading a school book like the little nerd he is.

"When did I even come home?"

"I don't know. I didn't even hear you come in and you know that I guard that door like crazy when you're gone."

Dean swings his legs out of the bed, finding he's wearing his boxers and that wifebeater he put on to go to work last night. It's a bit askew, but that might very well be because he's far from an immobile sleeper. His jeans are over a chair and if he's not mistaken, there's even money peeking out of one pocket.

"Phh, you probably forgot to lock it." He's frowning even as he's teasing his brother, because nothing adds up here.

"I didn't forget to lock it. I'm just astounded you managed to sneak in without breaking anything, like you usually do when you're drunk."

"I wasn't drunk."

He stretches and his muscles pop in the most delicious way. His body feels good, no soreness, no nausea, not even a headache. What the fuck did he do last night that earned them money without a lingering feeling of shame and disgust and achy bits where he was shoved around? And there's no way he could have been drunk enough to lose time and still feel this good in the morning.

"You don't even remember coming home."

"Yeah, but-…" Besides, he'd never get that drunk while he still had to be alert enough to possibly protect Sammy. "Just don't go around telling Dad I was."

"You know I wouldn't. By the way, thank you for the play. I didn't even know they had a bookstore here. And it's even new and everything."

Dean casually picks up his jeans to look at the money in his pockets and almost forgets what they were talking about. _What_ did he _do_ last night?

"What play?"

Sam holds up a copy of 'Othello' and quirks his brow in an altogether self-satisfied way.

"Not drunk, huh?"

"Shut up, bitch."

"Jerk."

Dean is on his way to the bathroom when he hears:

"Besides, you have a massive hickey on your neck."


End file.
